Category Archives: Trip Building Anatomy

Trip planning can just be as exciting as the actual trip itself — and it can also be just as overwhelming! Our cruise ends just outside Rome, Italy on Saturday, July 22nd. We will take a taxi to the train station and then a train into Rome…and then??? Yeah, exactly. Rome is HUGE and some travelers can spend over a week there. We do not quite have that much time, but I do want to allow for enough time to see the major sites and not be on the constant Go-Go-Go. The first thing I had to decide on is where to stay. And after much research reading books, blogs and travel advice forums it seems to be the neighborhood of Travestere is where we will stay. It has a great location close to most attractions and has easy public transportation available. As for our days of sightseeing, I’ve decided on this rough outline:

Saturday 7/22: Taxi and train to hotel, check in by 5:00pm, walk around and check out the neighborhood

Sunday 7/23: Tour the Forum and Coliseum

Monday 7/24: Tour the Vatican and Sistine Chapel

Tuesday 7/25: Day trip to Tivoli and visit Villa D’Estate and Villa Adrianna

Wednesday 7/26: “Rest Day” – stroll the Pantheon and the Spanish Steps, both within a half hour walk of our hotel

Thursday 7/27: Depart Rome to ???

It seems like we have to much time in Italy, but the more I read up about places the more I find that “I want to go there too!” but there just isn’t enough days to do it all. I am also keeping an eye out for incredible cruise deals leaving from Rome. The cruises I am tracking haven’t had any fire sales that would change our plans, but I’ll definitely be on the lookout for the next several weeks for anything that comes up. As a matter of fact, there is a smoking good deal now, but we wouldn’t be able to catch our flight out of Milan and back to the US. Here is the deal:

11 day cruise on the Norwegian Spirit for a rock bottom fare of $590. Add in port and taxes and it comes to $776. Add in the tips/gratuities for the crew of $14 per person, per day and that comes to $154. Add everything up and the total price is $930. Divide that by 11 days and it is around $84.50 per person, per day which definitely hits our sweet spot of cruise pricing. Here is the full itinerary:

We would book this cruise if it only arrived back to Rome a day before. As it stands, our flight leaves at 4:00pm on that Thursday from Milan and there are too many variables and possible setbacks that would prevent us from getting back to Milan on the same day. So as far as this vacation deal, we will have to pass.

I’ve spent the last few days trying to figure out a Marriott Category 1-5 property that Lisa and I can stay at for an entire week. This challenge is to utilize the Marriott Flight and Hotel package. Basically, I need to give Marriott 270,000 points and I’ll get to stay in a hotel for one week. As a bonus, Marriott will also credit my Southwest Airlines account with 120,000 miles. This is important because by getting 120,000 SW Air miles, that will automatically trigger a very sought-after reward offered by Southwest Airlines — the SW Airlines Companion Pass. This pass will allow me to book one ticket for myself, and a second passenger gets to fly with me for free. And if I time it just right and get my points in January, the pass will be good for almost two years. And with the number of routes that Southwest Airlines has available, this Companion Pass can really help Lisa and I travel all over the USA at a 50% discount. But first I have to determine if there are any Marriott properties that are in a place that we’d actually like to stay in for an entire week. The other part that has been hard is that there are not many Marriott Category 1-5 properties that sound appealing to stay at for one week — there are many Courtyard by Marriotts, but those are pretty basic rooms. We’d prefer to stay at the JW Marriott brands, but those usually category 8 hotels, which would require another 90,000 points at 360k. We don’t have enough points for that, and purchasing points would set us back about $525, which might not be so bad if the amenities and bonuses are too good to pass up! However, here is what I have come up with so far:

Residence Inn Palm Desert: it’s an extended stay hotel, so we’d have a small kitchen to do some cooking, plus it comes with a daily free breakfast. There’s plenty to do around the Palm Springs area, and we could go here for Spring Break.

Mexico City, Marriott Reforma Hotel. Or upgrade 30,000 points to the JW Marriott. The upgraded option would get us a daily breakfast and a very nice property. There is so much in Mexico City, so we definitely wouldn’t get bored. But could I actually convince Lisa that it is safe and worthy of a visit?

San Diego Residence Inn (multiple properties): sunny, warm weather of Southern California. Plenty to do in San Diego, La Jolla, Carlsbad, Oceanside, etc. However, we’ve pretty much ‘been there, done that’ so there wouldn’t be a whole lot new. But flights are cheap, quick and plentiful to San Diego, and we could just chill out and find new things to do.

So right now those are our three main options. Other possibilities include St Louis, Detroit, Indianapolis, Kansas City, Washington DC, Colorado Springs and Flagstaff. But many of those cities are probably good for four days max, so an extra three days might lead to a little boredom. And it’s a great problem to have. The ability to travel on points and maximize our rewards to get even more travel possibilities. I have until the end of March to figure out what would be the best place to go to and spend a week. A week just seems so long to be at for the entire time! But we’ll figure something out. If anything, we’ll just find a favorite people watching spot and park ourselves down to read and hang out like the locals.

Our tickets are booked for summer 2017 — New York, New York to Milan, Italy. We’ll have approximately five weeks to explore, but where should we go and what should we do? Reading up on Milan, I have discovered that it is a hub for no-frill airlines and is a jumping off point for all parts around Europe. While that is exciting and opens up the possibilities, it is also problematic because it opens up so many possibilities. Now, instead of focusing on Italy, we could potentially look at the entire map of Europe and figure out where to go!

Alas, after doing more reading on Italy, Milan is only a three-hour train ride to Venice. And after further research, I found a cruise that leaves Venice and goes around Italy to end up in Rome. Better yet: the itinerary is ideal and the price is jaw-dropping. Our cruise budget is around $100 per person, per day. This $100 per day is for the basic cruise fare plus port fees and taxes. Ideally, it would also include gratuity at $13.50 per person, per day, but lately we have realized that those parameters are very difficult to find. Yes, sometimes we’ll see a deal where tips are included and/or there might be an onboard ship credit. But for $100 or less per person per day, it is not often.

Well, we’ve found a deal that includes cruise fare, port and taxes, tips and some onboard spending money for under $100 per person, per day. Details:

The sailing is on the Celebrity Constellation, an older ship that we are very familiar with because we have sailed on her sister the Millennium. We like the Celebrity product, ranking it our second favorite cruise line. As a matter of fact, my first ever cruise was on a Celebrity ship — the Mercury.

This covers our room, food, onboard entertainment and activities, plus of course the transportation to take us to six different cities. And we’ll debark our cruise just outside of Rome, so we can continue our travels in Rome and then make our way north through Tuscany and Cinque Terre en route back to Milan. And who knows? Maybe another great cruise deal will pop up that will be hard to pass up.

So for now, we have a cruise booked and then two and a half weeks that are open for the possibilities. We have plenty of time to make plans — it is always exciting to read about places that we could go to, and then make plans to actually get there! Stay tuned…

With our Emirates flight booked, we just need to find flights to and from New York. It seems a little early to book, and the fares are a little more than I want — around $300 per person, each way on various airlines, or about $1200. Discount airline Southwest is an option, but their schedule is only open until May 8th, 2017. So other options:

Use the Alaska Airlines companion fare for $121. Lisa pays the regular round trip fare, and then I pay just $121. Current Alaska Airlines single fare is $540, so with the companion fare the total would be around $665. Not bad, but I know that I can do better.

Use my Ritz-Carlton Visa card and make my reservation through their discount air portal. I can book with most major airlines except Southwest, Spirit and Frontier. Using their service will give me a $100 discount for two, round-trip tickets. Using the Alaska scenario above, two tickets at $540 and minus $100 will give me a total price of $980.

Use my Citi Thank You Points. I have 50,000 points, and using their booking engine I can book American Airline tickets at 1.6 value. That means every Thank You point is valued at 1.6 cents, giving me 50k x .016 = $800. So if I find tickets on American Airlines that would cost $600 in real money, I can use 37,500 Thank You points.

Use my Chase Ultimate Rewards to either transfer points to an airline mileage club or use the web travel portal and book directly. I have 50k points, which equals $500 towards airfare.

Use my Delta Airlines Skymiles to book an award ticket. I have 25k miles, which is enough for two one-way tickets at 12,500 points each.

After evaluating all our options, I decided to go ahead and book the first leg of our trip to New York using Delta Airlines award miles for two one-way tickets. We will take a red eye flight leaving at 12:50am on Monday, July 3rd and after a connecting flight in Minneapolis, we will arrive at JFK at 11:00am. That will give us the rest of Monday, all of Tuesday and part of Wednesday to enjoy New York. I am particularly interested in seeing some fireworks over the Statue of Liberty, but we’ll have to be smart and look for a hotel that might be able to offer views and a reasonable cost for two nights.

Lisa and I have been to New York a few times before so there is nothing “must-see” that is on a bucket list, but we would like to check out the Guggenheim Museum, the Met and/or maybe do one of those touristy open air bus tours. We’ll see. The most important thing though is that we gave ourselves enough time to arrive to New York a couple of days before our international flight, so any airline delays or cancellations should be mitigated enough for us to make the Milan flight, knock on wood.

So there you have it. We are slowly building our summer plans by booking our major transportation — we still have return flights from New York to take care of, but we have plenty of time and we still have a number of possibilities on what we might want to do in New York when we get back and for how long. So far the trip this trip has costed $895 + $5.60 = $901.06.

Our 2017 summer is wide open. Make that, was, wide open. Lisa has a trip to the East Coast with her eighth grade students, and is set to return by June 30th. That means that we have the rest of July and part of August to plan a vacation. I was content to just not book anything and wait for any last minute deals to come along, giving us a bit of freedom and mystery as to where we were to go. But alas, I received an email this morning from Emirates Airlines with a deal that was just too good to pass up.

Round trip flights for two people for just $899 during the peak summer season. The catch? It was only valid from New York City’s JFK airport to Milan, Italy. Milan, let alone Italy, wasn’t really on my radar for a place to travel to. I was thinking more the United Kingdom or France. But hey, Italy! Sure, if the price is right, let’s do it. And so I researched the flights and did my due diligence by the following:

The promotion stated that there were also flights available from Portland and Seattle for around $1400, with other fine print restrictions, including all flights would have to go through JFK and on to Milan. So I checked on flights from Portland to Milan or Seattle to Milan. The best price was too much to consider — $2500 round trip.

I priced nonstop direct flights from Portland to Europe general on Delta, Lufthansa and Icelandair. Again, nothing attractive.

Finally, I used hipmunk.com and Google flights for flights all over Europe. The best was still around $1700, still too much for what I wanted to pay.

The Emirates deal was still available when I searched for their JFK – Milan flights, departing July 5th and returning on August 10th. That’s exactly five weeks to spend in Europe. And upon further investigation, apparently Milan is a hub for discount airlines that fly all over Europe. So conceivably, we could just be flexible and scope out deals for other European cities and then just take a cheap flight there from Milan.

Thus, a round trip flight for two people on a great airline for $899 was a no-brainer. We just have to find round trip flights to New York from Portland, which I don’t think will be too much of an issue. Between Southwest Airlines and our Alaska Airlines $121 companion fare, I figure that the most we would spend out of pocket is $600. Together that will be $1500 to fly to Europe and back in the peak of summer. That is just too good a deal to pass up, so I booked the flight. Hello, Italy, here we come!